Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home’s striking presence is undeniable. A porte-cochère welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef’s kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home’s most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the home’s entertainment offerings. The seamless connection between indoor and outdoor living is one of the home’s greatest attributes. Heated pool, hot tub and fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.
Active
Listed by: Four Seasons Sotheby's Int'l Realty
Price cut: $500.5K (1/1)
$3,995,000
816 Black Bear Road, Jamaica, VT 05343
4beds
5,500sqft
Est.:
Single Family Residence
Built in 2010
44.47 Acres Lot
$-- Zestimate®
$726/sqft
$-- HOA
What's special
Stunning viewsHeated poolPrivate movie theaterVast mountain viewsWarm rustic eleganceTimber-framed architectureWide oak floors
- 390 days |
- 1,309 |
- 47 |
Zillow last checked: 7 hours ago
Listing updated: February 17, 2026 at 06:24pm
Listed by:
Betsy Wadsworth,
Four Seasons Sotheby's Int'l Realty 802-464-1200
Source: PrimeMLS,MLS#: 5030672
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Heating
- Propane, Solar, Heat Pump, Zoned, Radiant Floor
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Dual Fuel Range, Exhaust Fan
- Laundry: 1st Floor Laundry, In Basement
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Hearth, In-Law Suite, Kitchen Island, Kitchen/Living, Primary BR w/ BA, Natural Light, Natural Woodwork, Vaulted Ceiling(s), Walk-In Closet(s), Walk-in Pantry
- Flooring: Carpet, Ceramic Tile, Hardwood, Tile, Wood
- Windows: Blinds, Drapes
- Basement: Finished,Walk-Out Access
- Has fireplace: Yes
- Fireplace features: Wood Burning
Interior area
- Total structure area: 5,500
- Total interior livable area: 5,500 sqft
- Finished area above ground: 5,500
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Paved
- Garage spaces: 6
Features
- Levels: 2.5
- Stories: 2.5
- Patio & porch: Patio, Covered Porch
- Exterior features: Deck, Garden
- Has private pool: Yes
- Pool features: In Ground
- Has spa: Yes
- Spa features: Heated
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 44.47 Acres
- Features: Country Setting, Landscaped, Orchard(s), Recreational, Ski Area, Trail/Near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails
Details
- Parcel number: 32410111593
- Zoning description: No zoning
- Other equipment: Standby Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Craftsman
- Property subtype: Single Family Residence
Materials
- Timber Frame, Wood Siding
- Foundation: Concrete
- Roof: Metal,Standing Seam
Condition
- New construction: No
- Year built: 2010
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Septic Tank
- Utilities for property: Propane
Green energy
- Energy efficient items: HVAC, Water Heater
- Energy generation: Solar
- Indoor air quality: Ventilation
Community & HOA
Community
- Security: Security System, Hardwired Smoke Detector
Location
- Region: Jamaica
Financial & listing details
- Price per square foot: $726/sqft
- Tax assessed value: $1,722,400
- Annual tax amount: $41,949
- Date on market: 3/1/2025
Estimated market value
Not available
Estimated sales range
Not available
$6,612/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/1/2026 | Price change | $3,995,000-11.1%$726/sqft |
Source:  PrimeMLS #5030672 Report a problem | ||
| 3/1/2025 | Listed for sale | $4,495,500+71.8%$817/sqft |
Source: PrimeMLS #5030672 Report a problem | ||
| 6/16/2015 | Sold | $2,617,000$476/sqft |
Source: Public Record Report a problem | ||
| 11/21/2013 | Sold | $2,617,000$476/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $1,722,400 |
| 2023 | -- | $1,722,400 |
| 2022 | -- | $1,722,400 |
| 2021 | -- | $1,722,400 |
| 2020 | -- | $1,722,400 |
| 2019 | -- | $1,722,400 |
| 2018 | -- | $1,722,400 +6.1% |
| 2017 | -- | $1,623,300 |
| 2016 | -- | $1,623,300 +9900% |
| 2015 | -- | $16,233 +2.3% |
| 2014 | -- | $15,874 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$26,828/mo
Principal & interest
$20602
Property taxes
$6226
More affordability tools
Climate risks
Neighborhood: 05343
Getting around
0 / 100
Car-DependentNearby schools
GreatSchools rating
- NAWardsboro Central SchoolGrades: PK-6Distance: 2.9 mi
- 3/10Leland & Gray Uhsd #34Grades: 6-12Distance: 8.5 mi
Schools provided by the listing agent
- Elementary: Jamaica Village School
- Middle: Leland Gray Union Middle/High
- High: Leland Gray
- District: Windham Central
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 05343
- Vermont
- Windham County
- Jamaica
- 05343
- 816 Black Bear Road
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